City Streets (1931)

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Gary Cooper is cast as a racketeer known only as The Kid. He has chosen a life of crime out of love for Nan (Sylvia Sidney), the daughter of mob henchman Pop Cooley (Guy Kibbee). Eventually railroaded into prison by her crooked cohorts, Nan implores The Kid to give up the rackets, but he refuses. Things go downhill very rapidly after that, culminating with The Kid and Nan being taken "for a ride"